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Highly Stereoselective One-Pot Synthesis of Bicyclic Isoxazolidines with Five Stereogenic Centers by an Organocatalytic Process

Authors

  • Di Zhu,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Min Lu,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Lu Dai,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Guofu Zhong Prof. Dr.

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Research support from the Ministry of Education in Singapore (ARC12/07, no. T206B3225) and Nanyang Technological University (URC, RG53/07) is gratefully acknowledged. We thank Dr. Yongxin Li for the X-ray crystallographic analysis.

Abstract

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Fünf auf einen Streich! Eine neuartige, einfache und hoch stereoselektive Synthese der Titelverbindungen wird vorgestellt, bei der fünf stereogene Zentren mithilfe eines organokatalytischen asymmetrischen Eintopf-Tandemprozesses unter Beteiligung einer diastereoselektiven intramolekularen [3+2]-Nitron-Cycloaddition kontrolliert erzeugt werden (siehe Schema).

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